Photo by Shirley Rhodes

Holiday Rentals in Brattleboro

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Holiday Rentals in Brattleboro

Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (4)
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Property grounds
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
10.0 out of 10, Exceptional, (11)
"Beautiful home with everything that we needed. Short drive to Landmark College to see our daughter and close to Brattleboro shopping and restaurants. The river was also wonderful to wake up to. Highly recommend! "
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
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Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (13)
"We had a very pleasant stay at Bear Creek Cabin. It’s just a short ride to Berkshire East for skiing and snow tubing. The house is beautiful and has all the essentials. Bunk room was perfect for the kids, and upstairs open master bedroom had beautiful views. We’d love to come back in the summer to enjoy the creek and warm weather activities. FYI- there are limited restaurant options in the immediate area, so we stopped for groceries on the way up. The kitchen had all we needed. Thanks for a...
The price is €571
includes taxes & fees
19 May - 20 May
Bear Creek Cabin
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (192)
"Our family rated this as our best stay in 7 years of traveling with VRBO properties. There was lots of room for everyone to spread-out, but the family spent most of the time in the game room playing pool, fuzzball, shuffleboard and Ping-Pong. Overall and great spring break for the family and friends."
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (28)
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Interior
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
10.0 out of 10, Exceptional, (29)
"We had a wonderful stay. The house has everything you need!"
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Exterior
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
10.0 out of 10, Exceptional, (27)
"This was one of the best locations we have stayed at! We came up for a fundraiser at Stratton Mountain. Tommy was so helpful and provided great information from booking up until checkout. There is a great virtual guide that answers all important questions. The house and outdoors were exactly what we were looking for. Our dog loved running around and we enjoyed the hot tub. The house was very clean and had all the necessities we needed. Our favorite part was being cozy on the coach watching...
Dream Stratton Forest Cabin w/Hot Tub & Fast WiFi
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
The price is €539
includes taxes & fees
6 Jun - 7 Jun
Mount Snow's Best View - Sleeps 8-10
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (39)
"We were visiting relatives and found Hickory Hill a really wonderful place to stay, both comfortable and pleasant. It is a working kennel so there were occasional barks but was very quiet at night- you can see both sunrise and sunset from the deck. The area has dark skies so the stars are really clear ... big improvement for us city folks. Very glad they board people in addition to pups! :)"
Spectacular Mountain views with all the amentities nearby
Fridge, microwave, stovetop, cookware/dishes/utensils
Cozy Treetop Hideaway Near Harriman Reservoir!
9.8 out of 10, Exceptional, (10)
"The house was a very cute ski cabin-y feeling vacation spot with a gorgeous view of the reservoir. Location was great- not too far from the center of Wilmington. And a drive through the mountains/National Forest away from the other cities/tourist areas near Bennington. It snowed while we were staying and the owners stayed on top of plowing so we could drive in and out - they weren't kidding about needing 4WD to get in and out in the winter. Overall, we'd come back in a heartbeat"
Cozy Treetop Hideaway Near Harriman Reservoir!
Smart TV, books
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (28)
"Super clean and tidy. Good location with 5 nearby ski mountains. The listing does not state that the indoor fireplace can not be used; so we were disappointed to discover that on arrival."
The price is €1,040
includes taxes & fees
18 May - 19 May
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Exterior
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (140)
"Great little house to enjoy spending time with family and all that VT has to offer. Wonderful host, we will be back."
The price is €339
includes taxes & fees
20 May - 21 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (116)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Fridge, microwave, oven, stovetop
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
9.6 out of 10, Exceptional, (44)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is €326
includes taxes & fees
21 May - 22 May
Family Friendly Hilltop House In Putney Vermont
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Brattleboro you may be interested in

Lobby
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very good, (900)
"Good stay "
The price is €137
includes taxes & fees
22 May - 23 May
Hampton Inn Brattleboro
Interior
Latchis Hotel
2.5 star property
8.4 out of 10, Very good, (565)
"It was a great experience. But extremely pricey for the quality of the room. "
The price is €142
includes taxes & fees
27 May - 28 May
Latchis Hotel
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, (1000)
"Accomodations were clean and room was nice. Property wedged between a McDonalds and a Wendy's. Good for a quick overnight"
The price is €79
includes taxes & fees
23 May - 24 May
The Covered Bridge Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Brattleboro holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Brattleboro holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Brattleboro holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Brattleboro holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Brattleboro. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Brattleboro holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Brattleboro holiday rentals we have selected for you start as low as €339 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Brattleboro rentals

At Expedia, we put the best Brattleboro holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Brattleboro rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Brattleboro holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Brattleboro. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Brattleboro?

Yes, there are holiday rentals in Brattleboro close to Brattleboro Bowl, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and ski slopes in Brattleboro. Leave some time to check out the shops and entertainment venues during your trip.

What are some of the best holiday rentals that Brattleboro has to offer?

Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly: This holiday home rental outside of Brattleboro offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Brattleboro?

Expedia has 16 holiday rentals for your stay in Brattleboro.

What can I see and do in Brattleboro?

Enjoy the outdoors at Brattleboro Common and Connecticut River, or simply take in cultural attractions like The Stone Church and Tasha Tudor Museum. Other places in town to visit include Latchis Theatre and Brattleboro Farmers' Market.

What’s a holiday rental in Brattleboro like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brattleboro. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.

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